The Biggest Failure From My Twenties: Becoming a High School Teacher

biggest failure of 20s

Some people just know what they’re meant to do. Ask them in their first year of college and they’ll outline their 15-year plan, with each of the steps they’ll take every week to make sure they’re on pace to get there. Ugh.

Don’t get me wrong—I’m really impressed by that kind of clarity and focus, but it’s definitely NOT what my experience was like. Luckily, I know I’m not the only one who didn’t have my career path set in stone the moment I graduated.

Guest writer Claire McCabe was a little indecisive in her years after college, but a sudden announcement from her parents prompted her to make a quick career decision—which she’s still paying for today. Read on to learn about Claire’s biggest career failure from her twenties—and her suggestions for how you can avoid making the same mistake.


I’ve experienced a myriad of career failures, but today I’m going to talk about just one—the biggest failure from my twenties.

As I contemplate the ups and downs of my career, I often wonder: How in the world could I have possibly thought it would be a good idea to teach high school at the tender young age of 24?

My decision to both apply to teacher school and pursue teaching came about when I was 23 and my parents informed me that they were cutting me off financially and that I needed to get a “real” job. Yes—just like that awful scene in Girls when Hannah’s parents tell her they won’t support her anymore. So, I made a major financial and career decision in the span of a single month. (Note: I don’t recommend this course of action.)

With minimal research, I applied to the UC Santa Cruz Master’s in Teaching program and got in, not paying any attention to the program or the outcomes. Mostly I just wanted to live in Santa Cruz so I could learn to surf. I also took out some loans to pay for the program.  (Note: I also don’t recommend this course of action).

I’ll never forget my first week of Teacher School: My old friend from high school came to visit me and I introduced her to a couple of my new friends in the program (we were going to a Tiffany concert at the Beach Boardwalk, natch). I think I had said something along the lines of, “I’m so excited to be a teacher!” and my friend, an established and wise educator who had worked with kids her whole life said, “But you hate kids!” In retrospect, this should have been somewhat of a red flag.

I sailed through the program without too much trouble or reflection. I had a couple “bad” days student teaching, which involved a few tears on my end, but I had a really great Master Teacher who held my hand (perhaps too much).

In my opinion, 24 isn’t a great age to make huge life decisions. If anything, it’s a time where you should be testing things out, wading in the water, trying on careers like you try on clothes. Getting internships, talking to people, doing research.

Instead, I decided that Santa Cruz was too small of a town and that I needed to move to San Francisco after completing my program. I applied for and accepted the first job I found, one that was teaching high school English in East Oakland.

I won’t spend too much time explaining the obvious—that I was unprepared to start my teaching career in a dangerous part of Oakland in an underfunded school filled with at-risk kids who had little support at home and came from really difficult life situations. I wasn’t the teacher they needed, and the kids knew that. I was barely able to get through lesson plans, terrible at disciplining students, had no classroom management, and—worst of all—wasn’t sure I wanted to be a teacher or be there at all.

Other teachers at the school, teachers who were 150% dedicated to their craft and their jobs, realized I was a terrible fit for the job and turned their backs on me. My “Master Teacher,” the teacher who was supposed to be my mentor, was only one year older than me and only visited my classroom a handful of times that year. She was so overwhelmed with her own classes and workload that she didn’t have time to be more involved.

My stress level was so off the charts that I stopped eating and lost ten pounds. Friends and family members expressed concern. I must have looked so miserable (I was only getting a few hours’ sleep a night) that it was easy to say, “She doesn’t like where she works.”

If there was ever an experience that would make you want to quit teaching, this was it. So when the school year came to an end, I gave my notice. I may have been miserable, but I was determined to make it through the year. As a side note, other teachers had not—there were several who had resigned earlier in the year.

Now that I’m in my thirties, I sometimes regret giving up so easily. I wonder if now I could have handled it with more life experience and at an easier school. It’s hard to say, but I walked away from a career that I was definitely not ready for at the time. Now when someone tells me they’re a teacher, I buy them a drink and say, “Hats off to you” with a little bit of envy and much respect.

So don’t do what I did. Research your career path, your workplace, and know thyself enough before you commit to a career that is over your head. If you don’t know what you want to do, talk to a career counselor and get some insight into yourself before you undertake something as big as teaching. The same goes for law school, med school, and any other graduate education that requires a major financial commitment.

I may have kissed teaching goodbye years ago, but those loans? I’m still paying them off!

Homework time! Claire mentions trying on a career before you commit to a major financial and time investment, like grad school. Look for ways you can do this, like conducting informational interviews, job shadowing, or volunteering in your area of interest.


2 Responses to “The Biggest Failure From My Twenties: Becoming a High School Teacher”

  1. Mary

    Substitute teaching is a great alternative! You get to enjoy the best of what teaching should be all about, without all of the negative aspects of full time teaching that eventually drives some teachers out of the profession. You make less money as a substitute, but hey, at least you still get to have a life. Every day is a new adventure, you go to work happy, go home happy, and are insulated from all of those damn school politics that stress the heck out of full-time teachers. Anyway, it is not about how much you make, it’s about how well you manage what you make. As long as you don’t live beyond your means, you’ll be fine.


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